ES2964692T3 - Nanofibras antibacterianas - Google Patents
Nanofibras antibacterianas Download PDFInfo
- Publication number
- ES2964692T3 ES2964692T3 ES16787182T ES16787182T ES2964692T3 ES 2964692 T3 ES2964692 T3 ES 2964692T3 ES 16787182 T ES16787182 T ES 16787182T ES 16787182 T ES16787182 T ES 16787182T ES 2964692 T3 ES2964692 T3 ES 2964692T3
- Authority
- ES
- Spain
- Prior art keywords
- nanofibers
- alginate
- calcium
- silver
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000002121 nanofiber Substances 0.000 title claims abstract description 475
- 230000000844 anti-bacterial effect Effects 0.000 title abstract description 132
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 claims abstract description 104
- 229940072056 alginate Drugs 0.000 claims abstract description 103
- 235000010443 alginic acid Nutrition 0.000 claims abstract description 103
- 229920000615 alginic acid Polymers 0.000 claims abstract description 103
- 239000004332 silver Substances 0.000 claims abstract description 85
- 229910052709 silver Inorganic materials 0.000 claims abstract description 85
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims abstract description 78
- 239000006096 absorbing agent Substances 0.000 claims abstract description 75
- 238000000034 method Methods 0.000 claims abstract description 54
- 229920000858 Cyclodextrin Polymers 0.000 claims abstract description 18
- 239000000243 solution Substances 0.000 claims description 198
- 238000011282 treatment Methods 0.000 claims description 81
- -1 silver ions Chemical class 0.000 claims description 75
- 230000000845 anti-microbial effect Effects 0.000 claims description 52
- 230000002787 reinforcement Effects 0.000 claims description 50
- 239000000835 fiber Substances 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 44
- 238000001523 electrospinning Methods 0.000 claims description 40
- 239000003960 organic solvent Substances 0.000 claims description 36
- 239000000126 substance Substances 0.000 claims description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- 239000003242 anti bacterial agent Substances 0.000 claims description 20
- OKHHGHGGPDJQHR-YMOPUZKJSA-L calcium;(2s,3s,4s,5s,6r)-6-[(2r,3s,4r,5s,6r)-2-carboxy-6-[(2r,3s,4r,5s,6r)-2-carboxylato-4,5,6-trihydroxyoxan-3-yl]oxy-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylate Chemical compound [Ca+2].O[C@@H]1[C@H](O)[C@H](O)O[C@@H](C([O-])=O)[C@H]1O[C@H]1[C@@H](O)[C@@H](O)[C@H](O[C@H]2[C@H]([C@@H](O)[C@H](O)[C@H](O2)C([O-])=O)O)[C@H](C(O)=O)O1 OKHHGHGGPDJQHR-YMOPUZKJSA-L 0.000 claims description 20
- 239000004599 antimicrobial Substances 0.000 claims description 18
- 235000010410 calcium alginate Nutrition 0.000 claims description 18
- 239000000648 calcium alginate Substances 0.000 claims description 18
- 229960002681 calcium alginate Drugs 0.000 claims description 18
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 16
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 claims description 14
- 239000007864 aqueous solution Substances 0.000 claims description 14
- 229910001424 calcium ion Inorganic materials 0.000 claims description 13
- 159000000007 calcium salts Chemical class 0.000 claims description 11
- 230000007423 decrease Effects 0.000 claims description 10
- 238000000151 deposition Methods 0.000 claims description 10
- 210000000416 exudates and transudate Anatomy 0.000 claims description 10
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 claims description 8
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 8
- 238000005406 washing Methods 0.000 claims description 8
- 239000011248 coating agent Substances 0.000 claims description 7
- 238000000576 coating method Methods 0.000 claims description 7
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims description 7
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical group [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 6
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000005708 Sodium hypochlorite Substances 0.000 claims description 6
- XEFQLINVKFYRCS-UHFFFAOYSA-N Triclosan Chemical compound OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl XEFQLINVKFYRCS-UHFFFAOYSA-N 0.000 claims description 6
- 230000003115 biocidal effect Effects 0.000 claims description 6
- 229960003260 chlorhexidine Drugs 0.000 claims description 6
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 6
- 239000012286 potassium permanganate Substances 0.000 claims description 6
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 6
- 229960003500 triclosan Drugs 0.000 claims description 6
- 229910021607 Silver chloride Inorganic materials 0.000 claims description 5
- 239000001110 calcium chloride Substances 0.000 claims description 5
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 5
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 claims description 5
- FFTVPQUHLQBXQZ-KVUCHLLUSA-N (4s,4as,5ar,12ar)-4,7-bis(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1C2=C(N(C)C)C=CC(O)=C2C(O)=C2[C@@H]1C[C@H]1[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]1(O)C2=O FFTVPQUHLQBXQZ-KVUCHLLUSA-N 0.000 claims description 4
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 claims description 4
- GSDSWSVVBLHKDQ-UHFFFAOYSA-N 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)COC3=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-UHFFFAOYSA-N 0.000 claims description 4
- UNMYWSMUMWPJLR-UHFFFAOYSA-L Calcium iodide Chemical compound [Ca+2].[I-].[I-] UNMYWSMUMWPJLR-UHFFFAOYSA-L 0.000 claims description 4
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 claims description 4
- 229930182566 Gentamicin Natural products 0.000 claims description 4
- 239000004098 Tetracycline Substances 0.000 claims description 4
- 229910001622 calcium bromide Inorganic materials 0.000 claims description 4
- WGEFECGEFUFIQW-UHFFFAOYSA-L calcium dibromide Chemical compound [Ca+2].[Br-].[Br-] WGEFECGEFUFIQW-UHFFFAOYSA-L 0.000 claims description 4
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 claims description 4
- 229910001634 calcium fluoride Inorganic materials 0.000 claims description 4
- 229940046413 calcium iodide Drugs 0.000 claims description 4
- 229910001640 calcium iodide Inorganic materials 0.000 claims description 4
- 238000007787 electrohydrodynamic spraying Methods 0.000 claims description 4
- 229960002518 gentamicin Drugs 0.000 claims description 4
- 229960000282 metronidazole Drugs 0.000 claims description 4
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 claims description 4
- 229960004023 minocycline Drugs 0.000 claims description 4
- 229960001699 ofloxacin Drugs 0.000 claims description 4
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 claims description 4
- 229940071536 silver acetate Drugs 0.000 claims description 4
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 claims description 4
- 229910001961 silver nitrate Inorganic materials 0.000 claims description 4
- YPNVIBVEFVRZPJ-UHFFFAOYSA-L silver sulfate Chemical compound [Ag+].[Ag+].[O-]S([O-])(=O)=O YPNVIBVEFVRZPJ-UHFFFAOYSA-L 0.000 claims description 4
- 229910000367 silver sulfate Inorganic materials 0.000 claims description 4
- LMEWRZSPCQHBOB-UHFFFAOYSA-M silver;2-hydroxypropanoate Chemical compound [Ag+].CC(O)C([O-])=O LMEWRZSPCQHBOB-UHFFFAOYSA-M 0.000 claims description 4
- 229960002180 tetracycline Drugs 0.000 claims description 4
- 229930101283 tetracycline Natural products 0.000 claims description 4
- 235000019364 tetracycline Nutrition 0.000 claims description 4
- 150000003522 tetracyclines Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 abstract description 8
- 229940097362 cyclodextrins Drugs 0.000 abstract description 4
- 206010052428 Wound Diseases 0.000 description 81
- 208000027418 Wounds and injury Diseases 0.000 description 81
- 239000011575 calcium Substances 0.000 description 77
- 229920001222 biopolymer Polymers 0.000 description 70
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 67
- 229910052791 calcium Inorganic materials 0.000 description 61
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 60
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 52
- 235000010413 sodium alginate Nutrition 0.000 description 52
- 239000000661 sodium alginate Substances 0.000 description 52
- 229940005550 sodium alginate Drugs 0.000 description 52
- 235000019645 odor Nutrition 0.000 description 50
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 48
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 29
- 239000004094 surface-active agent Substances 0.000 description 24
- 238000010521 absorption reaction Methods 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 17
- 239000002245 particle Substances 0.000 description 16
- 239000001768 carboxy methyl cellulose Substances 0.000 description 13
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 13
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 13
- 238000005342 ion exchange Methods 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 12
- 239000004744 fabric Substances 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000011734 sodium Substances 0.000 description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000014759 maintenance of location Effects 0.000 description 8
- 238000001878 scanning electron micrograph Methods 0.000 description 8
- 101710134784 Agnoprotein Proteins 0.000 description 7
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
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- 238000002791 soaking Methods 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002250 absorbent Substances 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
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- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—Use of materials characterised by their function or physical properties
- A61L15/62—Compostable, hydrosoluble or hydrodegradable materials
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- A—HUMAN NECESSITIES
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- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/404—Biocides, antimicrobial agents, antiseptic agents
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- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/80—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a special chemical form
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- A61L2400/00—Materials characterised by their function or physical properties
- A61L2400/12—Nanosized materials, e.g. nanofibres, nanoparticles, nanowires, nanotubes; Nanostructured surfaces
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- Hematology (AREA)
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- General Health & Medical Sciences (AREA)
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- Materials For Medical Uses (AREA)
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| US201562154056P | 2015-04-28 | 2015-04-28 | |
| PCT/US2016/029862 WO2016176495A1 (en) | 2015-04-28 | 2016-04-28 | Antibacterial nanofibres |
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| ES2964692T3 true ES2964692T3 (es) | 2024-04-09 |
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| US (1) | US20180133359A1 (de) |
| EP (2) | EP3288600B1 (de) |
| JP (1) | JP6738833B2 (de) |
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| HK (1) | HK1250670A1 (de) |
| PL (1) | PL3288600T3 (de) |
| WO (1) | WO2016176495A1 (de) |
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| MX2020004744A (es) | 2017-11-09 | 2020-08-13 | 11 Health And Tech Limited | Sistema y metodo de monitoreo de ostomia. |
| KR102089086B1 (ko) * | 2018-08-10 | 2020-03-13 | 강원대학교산학협력단 | 항균성 금속 나노입자가 흡착된 나노섬유를 함유한 알긴산 히드로겔 및 이의 용도, 및 이를 제조하는 방법 |
| KR102071475B1 (ko) * | 2018-10-30 | 2020-03-02 | 윤대완 | 식품용 위생장갑 및 그 제조 방법 |
| USD893514S1 (en) | 2018-11-08 | 2020-08-18 | 11 Health And Technologies Limited | Display screen or portion thereof with graphical user interface |
| CN111996617B (zh) * | 2020-09-18 | 2023-03-21 | 青岛大学 | 一种耐火抗菌海藻纤维的制作方法 |
| CN112281257B (zh) * | 2020-10-22 | 2023-07-04 | 青岛大学 | 一种负载纳米氯化银的海洋纤维的制备方法 |
| CN114182529B (zh) * | 2020-11-17 | 2024-03-26 | 青岛尼希米生物科技有限公司 | 一种抗菌消臭纤维素纤维及其制备方法和应用 |
| IT202100002891A1 (it) * | 2021-02-10 | 2022-08-10 | Saati Spa | Composizioni polimeriche per la realizzazione di membrane nanofibrose per applicazioni cosmetico-medicali e procedimento per la loro realizzazione |
| CN115252874B (zh) * | 2022-08-18 | 2023-10-20 | 常州美杰医疗用品有限公司 | 一种可生物降解医用绷带及其制备方法 |
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| WO1992022285A1 (en) * | 1991-06-14 | 1992-12-23 | Viaderm Pharmaceuticals, Inc. | Alginate wound dressings |
| US5792090A (en) * | 1995-06-15 | 1998-08-11 | Ladin; Daniel | Oxygen generating wound dressing |
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-
2016
- 2016-04-28 CA CA2992999A patent/CA2992999A1/en active Pending
- 2016-04-28 PL PL16787182.1T patent/PL3288600T3/pl unknown
- 2016-04-28 US US15/570,276 patent/US20180133359A1/en active Pending
- 2016-04-28 CN CN201680038288.9A patent/CN107708754B/zh active Active
- 2016-04-28 EP EP16787182.1A patent/EP3288600B1/de active Active
- 2016-04-28 JP JP2017556548A patent/JP6738833B2/ja active Active
- 2016-04-28 EP EP23193492.8A patent/EP4252786A3/de active Pending
- 2016-04-28 ES ES16787182T patent/ES2964692T3/es active Active
- 2016-04-28 AU AU2016256436A patent/AU2016256436B2/en active Active
- 2016-04-28 BR BR112017023392A patent/BR112017023392A2/pt not_active Application Discontinuation
- 2016-04-28 WO PCT/US2016/029862 patent/WO2016176495A1/en unknown
-
2018
- 2018-08-09 HK HK18110213.0A patent/HK1250670A1/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2992999A1 (en) | 2016-11-03 |
| JP6738833B2 (ja) | 2020-08-12 |
| EP3288600A1 (de) | 2018-03-07 |
| HK1250670A1 (zh) | 2019-01-11 |
| EP3288600B1 (de) | 2023-09-06 |
| EP4252786A3 (de) | 2023-11-15 |
| EP3288600A4 (de) | 2019-01-02 |
| JP2018515193A (ja) | 2018-06-14 |
| AU2016256436A1 (en) | 2017-11-09 |
| BR112017023392A2 (pt) | 2018-07-17 |
| AU2016256436B2 (en) | 2020-10-22 |
| EP4252786A2 (de) | 2023-10-04 |
| PL3288600T3 (pl) | 2024-02-19 |
| CN107708754B (zh) | 2021-08-06 |
| CN107708754A (zh) | 2018-02-16 |
| US20180133359A1 (en) | 2018-05-17 |
| EP3288600C0 (de) | 2023-09-06 |
| WO2016176495A1 (en) | 2016-11-03 |
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